Portfolio assessment is a valid and reliable method to assess experiential learning. Developing a fully online portfolio assessment program is neither easy nor inexpensive. The institution seeking to take its portfolio assessment program online must make a commitment to its students by offering the technologies most suited to meet students' needs. Kaplan University developed and implemented a software solution that provides students with a custom, user-friendly experience while also meeting the requirements of their rigorous assessment process. This article presents some helpful tips for developing software to provide a desirable user experience to all parties involved with the portfolio assessment process: students, evaluators, and administrators.